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(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → tert-Butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate

HRID 993415
ノート
印刷プレビュー

反応式

HRID 993415 の反応式
[Cl:1][CH2:2][C@@H:3]([OH:15])[CH2:4][C:5](=[O:14])[CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O>P([O-])([O-])([O-])=O>[Cl:1][CH2:2][C@@H:3]([OH:15])[CH2:4][C@@H:5]([OH:14])[CH2:6][C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 7022053tert-butyl (5S)-6-chloro-5-hydroxy-3-oxohexanoate

生成物 1

HCID 9816157tert-Butyl (3R,5S)-6-chloro-3,5-dihydroxyhexanoate

試薬・触媒・溶媒 1

HCID 1061Phosphate溶媒

反応条件

温度
30 °C

実験手順

Sakaguchi flasks of 500 mL capacity were respectively charged with 50 mL of said medium A and, after sterilization, inoculated with the microbial strains indicated in Table 1, respectively. Aerobic shake culture was then carried out at 30° C. for 2 days. From each of the culture broths, the cells were harvested by centrifugation and suspended in 25 mL of 50 mM phosphate buffer (pH 6.5) containing 1% of tert-butyl(5S)-6-chloro-5-hydroxy-3-oxohexanoate (synthesized by the process described in Example 1) and 2% of glucose. The suspension was put in a 500 mL Sakaguchi flask and a reaction was conducted under shaking at 30° C. for 20 hours. After completion of the reaction, the reaction mixture was extracted twice with one volume of ethyl acetate each and the ethyl acetate phase was analyzed by high performance liquid chromatography (column: Nakalai-Tesque, Cosmocil 5CN-R (4.6 mm×250 mm), eluent: 1 mM phosphoric acid/H2O:acetonitrile=5:1, flow rate 0.7 mL/min., detection: at 210 nm, column temperature: 30° C.) for reaction rate and for the diastereomer ratio of the product tert-butyl(3R,5S)-6-chloro-3,5-dihydroxyhexanoate. The results are shown in Table 1.

後処理

  1. additionSakaguchi flasks of 500 mL capacity were respectively charged with 50 mL of said medium A
  2. customsynthesized by the process
  3. customAfter completion of the reaction
  4. extractionthe reaction mixture was extracted twice with one volume of ethyl acetate each and the ethyl acetate phase
  5. customwas analyzed by high performance liquid chromatography (column: Nakalai-Tesque, Cosmocil 5CN-R (4.6 mm×250 mm), eluent: 1 mM phosphoric acid/H2O:acetonitrile=5:1, flow rate 0.7 mL/min., detection: at 210 nm, column temperature: 30° C.) for reaction rate and for the diastereomer ratio of the product tert-butyl(3R,5S)-6-chloro-3,5-dihydroxyhexanoate

出典と根拠

ORDレコード
ord-d945e0f3f12d401289c13b53503fb669
出典データセット
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06472544B1

反応ノート

読み込み中…

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